Bilska-Markowska Monika, Kaźmierczak Marcin
Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland.
Centre for Advanced Technologies, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 10, 61-614 Poznań, Poland.
Org Biomol Chem. 2023 Feb 8;21(6):1095-1120. doi: 10.1039/d2ob01969h.
Selective introduction of a double bond motif into a multifunctional organic compound is always a big challenge. The Horner-Wadsworth-Emmons reaction is one of the most reliable, simple, and stereoselective olefination methods, widely used in organic chemistry. To the best of our knowledge, no review article on the application of HWE reaction in the synthesis of fluoroorganic compounds with direct biological interest has been published in recent years. The importance of the HWE reaction should be emphasised due to its simplicity and stereoselectivity. Under mild conditions and in one step, valuable compounds can be obtained. The HWE reaction is primarily a great tool in the synthesis of fluoroolefins that are, among others, peptide bond mimetics. Therefore, it can serve as an indispensable approach to access peptide bioisosteres and, consequently, analogues of numerous enzyme inhibitors. The protocol may be utilized to obtain florinated vinylphosphonate, vinylsulfone or sulfonate derivatives, which exhibit biological activity. In this review article, we would like to summarize the HWE reaction output of the last 12 years (since 2010).
将双键基序选择性引入多功能有机化合物始终是一项巨大挑战。霍纳-沃兹沃思-埃蒙斯反应(Horner-Wadsworth-Emmons reaction)是最可靠、简单且具有立体选择性的烯烃化方法之一,在有机化学中广泛应用。据我们所知,近年来尚未发表过关于霍纳-沃兹沃思-埃蒙斯反应在具有直接生物学意义的氟有机化合物合成中的应用的综述文章。鉴于其简单性和立体选择性,应强调霍纳-沃兹沃思-埃蒙斯反应的重要性。在温和条件下一步即可获得有价值的化合物。霍纳-沃兹沃思-埃蒙斯反应主要是合成氟烯烃(其中包括肽键模拟物)的一个重要工具。因此,它可作为获取肽生物电子等排体以及众多酶抑制剂类似物的不可或缺的方法。该方案可用于获得具有生物活性的氟化乙烯基膦酸酯、乙烯基砜或磺酸酯衍生物。在这篇综述文章中,我们将总结过去12年(自2010年以来)霍纳-沃兹沃思-埃蒙斯反应的成果。